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Anti-SARS-CoV-2 activity and cytotoxicity of Amaryllidaceae alkaloids from Hymenocallis littoralis

Ngoc-Thao-Hien Le, Steven De Jonghe, Kristien Erven, Tom Vermeyen, Aliou M. Baldé, Wouter A. Herrebout, Johan Neyts, Christophe Pannecouque, Luc Pieters and Emmy Tuenter
(2023) MOLECULES. 28(7).
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Abstract
The Amaryllidaceae species are well-known as a rich source of bioactive compounds in nature. Although Hymenocallis littoralis has been studied for decades, its polar components were rarely explored. The current phytochemical investigation of Amaryllidaceae alkaloids from H. littoralis led to the identification of three previously undescribed compounds: O-demethyl-norlycoramine (1), (-)-2-epi-pseudolycorine (2) and (+)-2-epi-pseudolycorine (3), together with eight known compounds: 6 alpha-hydroxyhippeastidine (4), 6 beta-hydroxyhippeastidine (5), lycorine (6), 2-epi-lycorine (7), zephyranthine (8), ungeremine (9), pancratistatin (10) and 9-O-demethyl-7-O-methyllycorenine (11). Among the eight previously reported compounds, five were isolated from H. littoralis for the first time (compounds 4, 5, 7, 8, and 9). Compounds 1, 4, 5, 7, 8, and 11 exhibited weak anti-SARS-CoV-2 activity (EC50 = 40-77 mu M) at non-cytotoxic concentrations. Assessment of cytotoxicity on the Vero-E6 cell line revealed lycorine and pancratistatin as cytotoxic substances with CC50 values of 1.2 mu M and 0.13 mu M, respectively. The preliminary structure-activity relationship for the lycorine-type alkaloids in this study was further investigated, and as a result ring C appears to play a crucial role in their anti-SARS-CoV-2 activity.
Keywords
Amaryllidaceae alkaloids, Hymenocallis littoralis, lycorine-type, galanthamine-type, DFT calculation, SARS-CoV-2, LYCORINE ALKALOIDS, NATURAL-PRODUCTS, ANTITUMOR

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MLA
Le, Ngoc-Thao-Hien, et al. “Anti-SARS-CoV-2 Activity and Cytotoxicity of Amaryllidaceae Alkaloids from Hymenocallis Littoralis.” MOLECULES, vol. 28, no. 7, 2023, doi:10.3390/molecules28073222.
APA
Le, N.-T.-H., De Jonghe, S., Erven, K., Vermeyen, T., Baldé, A. M., Herrebout, W. A., … Tuenter, E. (2023). Anti-SARS-CoV-2 activity and cytotoxicity of Amaryllidaceae alkaloids from Hymenocallis littoralis. MOLECULES, 28(7). https://doi.org/10.3390/molecules28073222
Chicago author-date
Le, Ngoc-Thao-Hien, Steven De Jonghe, Kristien Erven, Tom Vermeyen, Aliou M. Baldé, Wouter A. Herrebout, Johan Neyts, Christophe Pannecouque, Luc Pieters, and Emmy Tuenter. 2023. “Anti-SARS-CoV-2 Activity and Cytotoxicity of Amaryllidaceae Alkaloids from Hymenocallis Littoralis.” MOLECULES 28 (7). https://doi.org/10.3390/molecules28073222.
Chicago author-date (all authors)
Le, Ngoc-Thao-Hien, Steven De Jonghe, Kristien Erven, Tom Vermeyen, Aliou M. Baldé, Wouter A. Herrebout, Johan Neyts, Christophe Pannecouque, Luc Pieters, and Emmy Tuenter. 2023. “Anti-SARS-CoV-2 Activity and Cytotoxicity of Amaryllidaceae Alkaloids from Hymenocallis Littoralis.” MOLECULES 28 (7). doi:10.3390/molecules28073222.
Vancouver
1.
Le N-T-H, De Jonghe S, Erven K, Vermeyen T, Baldé AM, Herrebout WA, et al. Anti-SARS-CoV-2 activity and cytotoxicity of Amaryllidaceae alkaloids from Hymenocallis littoralis. MOLECULES. 2023;28(7).
IEEE
[1]
N.-T.-H. Le et al., “Anti-SARS-CoV-2 activity and cytotoxicity of Amaryllidaceae alkaloids from Hymenocallis littoralis,” MOLECULES, vol. 28, no. 7, 2023.
@article{01HAVV6K0GMD9S9STPJG6VKMDV,
  abstract     = {{The Amaryllidaceae species are well-known as a rich source of bioactive compounds in nature. Although Hymenocallis littoralis has been studied for decades, its polar components were rarely explored. The current phytochemical investigation of Amaryllidaceae alkaloids from H. littoralis led to the identification of three previously undescribed compounds: O-demethyl-norlycoramine (1), (-)-2-epi-pseudolycorine (2) and (+)-2-epi-pseudolycorine (3), together with eight known compounds: 6 alpha-hydroxyhippeastidine (4), 6 beta-hydroxyhippeastidine (5), lycorine (6), 2-epi-lycorine (7), zephyranthine (8), ungeremine (9), pancratistatin (10) and 9-O-demethyl-7-O-methyllycorenine (11). Among the eight previously reported compounds, five were isolated from H. littoralis for the first time (compounds 4, 5, 7, 8, and 9). Compounds 1, 4, 5, 7, 8, and 11 exhibited weak anti-SARS-CoV-2 activity (EC50 = 40-77 mu M) at non-cytotoxic concentrations. Assessment of cytotoxicity on the Vero-E6 cell line revealed lycorine and pancratistatin as cytotoxic substances with CC50 values of 1.2 mu M and 0.13 mu M, respectively. The preliminary structure-activity relationship for the lycorine-type alkaloids in this study was further investigated, and as a result ring C appears to play a crucial role in their anti-SARS-CoV-2 activity.}},
  articleno    = {{3222}},
  author       = {{Le, Ngoc-Thao-Hien and  De Jonghe, Steven and  Erven, Kristien and Vermeyen, Tom and Baldé, Aliou M. and  Herrebout, Wouter A. and  Neyts, Johan and  Pannecouque, Christophe and  Pieters, Luc and  Tuenter, Emmy}},
  issn         = {{1420-3049}},
  journal      = {{MOLECULES}},
  keywords     = {{Amaryllidaceae alkaloids,Hymenocallis littoralis,lycorine-type,galanthamine-type,DFT calculation,SARS-CoV-2,LYCORINE ALKALOIDS,NATURAL-PRODUCTS,ANTITUMOR}},
  language     = {{eng}},
  number       = {{7}},
  pages        = {{16}},
  title        = {{Anti-SARS-CoV-2 activity and cytotoxicity of Amaryllidaceae alkaloids from Hymenocallis littoralis}},
  url          = {{http://doi.org/10.3390/molecules28073222}},
  volume       = {{28}},
  year         = {{2023}},
}
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